EP4081297B1 - Tetrahydrobenzo-chinolinsulfonamidderivate als ige-modulatoren - Google Patents

Tetrahydrobenzo-chinolinsulfonamidderivate als ige-modulatoren Download PDF

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EP4081297B1
EP4081297B1 EP20841927.5A EP20841927A EP4081297B1 EP 4081297 B1 EP4081297 B1 EP 4081297B1 EP 20841927 A EP20841927 A EP 20841927A EP 4081297 B1 EP4081297 B1 EP 4081297B1
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optionally substituted
tetrahydrobenzo
alkyl
cyclopropyl
methylpropyl
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EP4081297A1 (de
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Timothy John Norman
Selvaratnam SUGANTHAN
Jag Paul Heer
Zeshan YOUSUF
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UCB Biopharma SRL
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Definitions

  • the present invention relates to tetrahydrobenzo-isoquinoline sulfonamide derivatives of formula (I), processes for preparing them, pharmaceutical compositions containing them and their use in treating disorders caused by IgE (such as allergic responses, non-allergic mast cell responses or certain autoimmune responses), and in particular disorders caused by the interaction of IgE with the Fc ⁇ RI receptor.
  • IgE such as allergic responses, non-allergic mast cell responses or certain autoimmune responses
  • IgE immunoglobulin E
  • IgE immunoglobulin E
  • IgE is secreted by, and expressed on the surface of, B-cells.
  • IgE synthesized by B-cells is anchored in the B-cell membrane by a transmembrane domain linked to the mature IgE sequence by a short membrane binding region.
  • IgE also is bound to B-cells (and monocytes, eosinophils and platelets) through its Fc region to a low affinity IgE receptor (Fc ⁇ RII).
  • Fc ⁇ RII low affinity IgE receptor
  • This IgE in turn is released into the circulation by the B-cells where it is bound by B-cells (through Fc ⁇ RII) and by mast cells and basophils through the so-called high affinity receptor (Fc ⁇ RI) found on the surface of the mast cells and basophils.
  • Fc ⁇ RI high affinity receptor
  • Such mast cells and basophils are thereby sensitized for allergen.
  • the next exposure to the allergen cross-links the Fc ⁇ RI on these cells and thus activate their release of histamine and other factors which are responsible for clinical hypersensitivity and anaphylaxis.
  • allergic diseases, urticaria, and asthma are usually treated with one or more of the following drugs: (1) antihistamines and antileukotrienes which antagonize the inflammatory mediators histamine and leukotrienes, (2) local or systemic (oral or injectable) corticosteroids or immunosuppressants which suppress a broad spectrum of inflammatory mechanisms, (3) short or long-acting bronchodilators which relax smooth muscle of constricted airway in asthma, or (4) mast cell stabilizers which inhibit the degranulation of mast cells that is normally triggered by IgE-binding at Fc ⁇ RI , (5) biologicals which prevent the binding of IgE at Fc ⁇ RI.
  • drugs (1) antihistamines and antileukotrienes which antagonize the inflammatory mediators histamine and leukotrienes, (2) local or systemic (oral or injectable) corticosteroids or immunosuppressants which suppress a broad spectrum of inflammatory mechanisms, (3) short or long-acting bronchodilators
  • EP 0 419 676 B1 discloses thionaphtalene derivatives having an immunoglobuline E antibody production suppressive action, and chemical mediator liberation inhibitory action, and useful as a therapeutical preparation for allergy symptoms such as bronchial asthma, allergic rhinitis, urticaria, anaphylaxy shock, atopic dermatitis, and hypersensitivity.
  • the present invention provides compounds of formula (I) and pharmaceutically acceptable salts thereof:
  • R1, R2 represents independently from each other a group chosen amongst:
  • the term "pharmaceutically acceptable salt” embraces salts of the compounds of formula (I) with a pharmaceutically acceptable acid or base, in particular an acid addition salt.
  • the acid addition salt form of a compound of formula (I) that occurs in its free form as a base can be obtained by treating the free base with an appropriate acid such as an inorganic acid, for example, a hydrohalic acid such as hydrochloric acid or hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid and the like; or an organic acid, such as, for example, acetic acid, trifluoroacetic acid, oxalic acid, hydroxyacetic acid, propanoic acid, lactic acid, pyruvic acid, malonic acid, succinic acid, maleic acid, fumaric acid, malic acid, tartaric acid, citric acid, methanesulfonic acid, ethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid,
  • the invention also relates to all stereoisomeric forms such as enantiomeric and diastereoisomeric forms of the compounds of formula (I) or mixtures thereof (including all possible mixtures of stereoisomers such as racemates).
  • reference to a compound or compounds is intended to encompass that compound in each of its possible isomeric forms and mixtures thereof, unless the particular isomeric form is referred to specifically.
  • each individual atom present in formula (I), or in formulae depicted herein may in fact be present in the form of any of its naturally occurring isotopes, with the most abundant isotope(s) being preferred.
  • each individual hydrogen atom present in formula (I), or in the formulae depicted herein may be present as a 1H, 2H (deuterium) or 3H (tritium) atom, preferably 1H.
  • each individual carbon atom present in formula (I) or in the formulae depicted herein, may be present as a 12C, 13C or 14C atom, preferably 12C.
  • the present invention includes within its scope solvates of the compounds of formula (I) above. Such solvates may be formed with common organic solvents or water.
  • the present invention also includes within its scope co-crystals of the compounds of formula (I) above.
  • co-crystal is used to describe the situation where neutral molecular components are present within a crystalline compound in a definite stoichiometric ratio.
  • the preparation of pharmaceutical co-crystals enables modifications to be made to the crystalline form of an active pharmaceutical ingredient, which in turn can alter its physicochemical properties without compromising its intended biological activity (see Pharmaceutical Salts and Co-crystals, ed. J. Wouters & L. Quere, RSC Publishing, 2012 ).
  • compounds of the invention are chosen amongst compounds of formula (I) wherein:
  • compounds of the invention are chosen amongst compounds of formula (I) wherein: R3 represents a group chosen amongst:
  • compounds of the invention are chosen amongst compounds of formula (I) wherein:
  • compounds of the invention are chosen amongst compounds of formula (I) wherein:
  • Another embodiment of the present invention concerns a pharmaceutical composition
  • a pharmaceutical composition comprising a detectable amount of a compound of formula (I) or a pharmaceutically acceptable salt, solvate or co-crystal thereof in combination with a pharmaceutically acceptable diluent or carrier.
  • the present invention concerns a compound of formula (I), a pharmaceutically acceptable salt, solvate or co-crystal thereof for use as a medicament, in particular for use in a method for the treatment or prevention of disorders caused by IgE, including allergy, type 1 hypersensitivity, familiar sinus inflammation, urticaria or related conditions, such as airway constriction in asthma, local inflammation in eczema, increased mucus secretion in allergic rhinitis, or increased vascular permeability.
  • disorders caused by IgE including allergy, type 1 hypersensitivity, familiar sinus inflammation, urticaria or related conditions, such as airway constriction in asthma, local inflammation in eczema, increased mucus secretion in allergic rhinitis, or increased vascular permeability.
  • compounds of the invention are chosen amongst:
  • 1,2,3,4-tetrahydronaphthalene (5.17 mL, 37.8 mmol) was added slowly to a suspension of AlCl 3 (10.6 g, 79.4 mmol) and prop-2-enoyl chloride (3.4 mL, 41.6 mmol) in DCM (300 mL) at -78 °C. The mixture was subsequently allowed to warm to room temperature overnight. The solution was carefully hydrolysed on ice and organic phase separated. The aq. phase was extracted twice with DCM and the combined organic fractions were washed with an aqueous solution of potassium carbonate and dried over sodium sulfate.
  • the resultant orange mixture was purged with N 2 for 5 min then heated at 120 °C for 11 hours after which further palladium (II) acetate (90 mg, 0.40 mmol) and tricyclohexylphosphonium tetrafluoroborate (400 mg, 1.05 mmol) were added and the mixture purged with N 2 for a further 5 min then heated at 120 °C for 3 days.
  • the reaction mixture was conc. in vacuo and the resiude taken up in EtOAc (400 mL containing a few millilitres of IPA). Water (150 mL) and brine (200 mL) were added and the phases separated.
  • the material was then buffer exchanged into Phosphate Buffered Saline (being, 137 mM NaCl, 2.7 mM KCI, 10 mM Na 2 HPO 4 , 1.8 mM K 2 HPO 4 , pH 7.4) and the material quantified and the degree of Tb conjugation determined by measuring the absorption at 280 nm and 343 nm.
  • Phosphate Buffered Saline being, 137 mM NaCl, 2.7 mM KCI, 10 mM Na 2 HPO 4 , 1.8 mM K 2 HPO 4 , pH 7.4
  • the integrity of the conjugated material was determined by analytical size exclusion chromatography on a S200 HR 10x300 column (GE Healthcare). Typical conjugation ratios were 4:1 Tb:lgE-Fc.
  • FRET reagents used were IgE labelled with Terbium (FRET donor), and soluble IgE receptor Fc ⁇ R1 ⁇ with a Y131A mutation, labelled with Alexa Fluor TM 488 (FRET acceptor). Unlabelled Fc ⁇ R1 ⁇ was also used to generate a background control.
  • the assay buffer consisted of 20mM Tris pH7.2, 150mM NaCl, and 0.002% Tween, 1% DMSO.
  • the assay was conducted according to the following: Each assay reaction was conducted in a volume of 25 ⁇ l in a 384-well half-volume plate. 10 point compound serial dilutions (3-fold) were generated in DMSO at a concentration of x50 that of the final assay concentration (FAC). Compound solutions were then prepared by IgE-Tb diluting 10-fold in assay buffer. For the assay, 5 ⁇ l of diluted compound was added to 10 ⁇ l of, followed by addition of 10 ⁇ l Fc ⁇ R1 ⁇ -Y131A-AF488. FRET reagents FACs were 5nM IgE-Tb, 25nM Fc ⁇ R1 ⁇ -Y131A-AF488.
  • the top FAC of compound in the assay was 10 ⁇ M.
  • the final DMSO concentration was 2%.
  • the maximum FRET signal (MAX) was measured in wells containing FRET reagents but no compound.
  • the assay was incubated for 2 hours at room temperature, protected from light and evaporation, and with gentle agitation.
  • FRET ratio was calculated as follows: Emission at 520 / Emission at 495 ⁇ 1000 .
  • the FRET ratio was used for the data analysis.
  • IC50 values for each compound were determined using four parameter logistic fit model using the XLFIT5 software package.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pulmonology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Claims (15)

  1. Verbindung der Formel (I) und pharmazeutisch unbedenkliche Salze davon:
    Figure imgb0037
     wobei
    R1, R2 unabhängig voneinander für eine aus den folgenden ausgewählte Gruppe stehen:
    Wasserstoff; oder NHC(O)NH-C1-6-Alkyl; oder NHSO2-C1-6-Alkyl; oder NHC(0)NH-Heteroaryl, gegebenenfalls substituiert durch ein oder mehrere R1a; oder Heteroaryl, gegebenenfalls substituiert durch eine oder mehrere Gruppen ausgewählt aus Amino; C1-6-Alkyl; C(O)O-C1-6-Alkyl; Nitril; Heteroaryl, gegebenenfalls substituiert durch ein oder mehrere R1a; NH-C1-6-Alkyl; NH-C1-6-Heterocycloalkyl; NH-C3-9-Cycloalkyl; NH-Heteroaryl, gegebenenfalls substituiert durch ein oder mehrere R1a;
    oder NH-Heteroaryl, gegebenenfalls substituiert durch eine oder mehrere Gruppen ausgewählt aus C1-6-Alkyl; C1-6-Hydroxyalkyl; C3-9-Hydroxyheterocycloalkyl;
    Heteroaryl, gegebenenfalls substituiert durch ein oder mehrere R1a; oder NHC(0)-C1-6-Alkyl; oder NHC(O)-Heteroaryl, gegebenenfalls substituiert durch ein oder mehrere R1a;
    R1a für eine aus den folgenden ausgewählte Gruppe steht: Halogen; Nitril; C1-6-Alkyl; C1-6-Halogenalkyl; C1-6-Alkoxy; C1-6-Halogenalkoxy; C(O)O-C1-6-Alkyl; C(O)OH;
    R3 für eine aus den folgenden ausgewählte Gruppe steht: C1-6-Alkyl, gegebenenfalls substituiert durch ein oder mehrere Gruppen ausgewählt aus R3a;
    C1-3-Alkandiyl-C3-6-cycloalkyl, gegebenenfalls substituiert durch ein oder mehrere R3a;
    C1-3-Alkandiyl-C3-6-heterocycloalkyl, gegebenenfalls substituiert durch ein oder mehrere R3a;
    C3-6-Heterocycloalkyl, gegebenenfalls substituiert durch ein oder mehrere R3a;
    C3-6-Cycloalkyl, gegebenenfalls substituiert durch ein oder mehrere R3a;
    R3a für eine aus Wasserstoff, Halogen, C1-2-Alkyl; Hydroxy; C1-2-Alkoxy ausgewählte Gruppe steht;
    R4 für eine aus den folgenden ausgewählte Gruppe steht: C3-6-Cycloalkyl, gegebenenfalls substituiert durch ein oder mehrere R4a-Gruppen; oder C1-6-Alkandiyl-C3-6-cycloalkyl, gegebenenfalls substituiert durch ein oder mehrere R4a-Gruppen; oder C1-6-Alkandiyl-C3-6-heterocycloalkyl, gegebenenfalls substituiert durch ein oder mehrere R4a-Gruppen;
    R4a für eine aus Hydroxy; Halogen; C1-2-Alkyl ausgewählte Gruppe steht.
  2. Verbindung nach Anspruch 1, wobei
    R1, R2 unabhängig voneinander für eine aus den folgenden ausgewählte Gruppe stehen:
    Wasserstoff; oder NH-Heteroaryl, gegebenenfalls substituiert durch eine oder mehrere Gruppen ausgewählt aus C1-6-Alkyl; Heteroaryl, gegebenenfalls substituiert durch ein oder mehrere R1a; oder Heteroaryl, gegebenenfalls substituiert durch ein oder mehrere Gruppen ausgewählt aus Amino; C(O)O-C1-6-Alkyl; Nitril;
    Heteroaryl, gegebenenfalls substituiert durch ein oder mehrere R1a; NH-C1-6-Alkyl; NH-C3-9-Heterocycloalkyl; NH-C3-9-Cycloalkyl; NH-Heteroaryl, gegebenenfalls substituiert durch ein oder mehrere R1a.
  3. Verbindung nach einem der vorhergehenden Ansprüche, wobei,
    wenn R1 von Wasserstoff verschieden ist, R2 für Wasserstoff steht;
    wenn R2 von Wasserstoff verschieden ist, R1 für Wasserstoff steht.
  4. Verbindung nach einem der vorhergehenden Ansprüche, wobei
    R3 für gegebenenfalls durch ein Fluoratom substituiertes C1-6-Alkyl steht
  5. Verbindung nach einem der vorhergehenden Ansprüche, wobei
    R4 für Cyclopropyl steht.
  6. Verbindung nach Anspruch 1, ausgewählt aus:
    3-Cyclopropyl-N-(2-methylpropyl)-7,8,9,10-tetrahydrobenzo[h]isochinolin-5-sulfonamid;
    1-[3-Cyclopropyl-5-(2-methylpropylsulfamoyl)-7,8,9,10-tetrahydrobenzo[h]isochinolin-7-yl]-3-ethylharnstoff;
    1-[3-Cyclopropyl-5-(2-methylpropylsulfamoyl)-7,8,9,10-tetrahydrobenzo[h]isochinolin-10-yl]-3-ethylharnstoff;
    3-Cyclopropyl-7-(methansulfonamido)-N-(2-methylpropyl)-7,8,9,10-tetrahydrobenzo[h]isochinolin-5-sulfonamid;
    3-Cyclopropyl-10-(methansulfonamido)-N-(2-methylpropyl)-7,8,9,10-tetrahydrobenzo[h]isochinolin-5-sulfonamid;
    3-Cyclopropyl-N-(2-fluor-2-methylpropyl)-7-[[6-(2-methyltetrazol-5-yl)pyridin-3-yl]amino]-7,8,9,10-tetrahydrobenzo[h]isochinolin-5-sulfonamid;
    3-Cyclopropyl-7-[3-[(2,5-dimethylpyrazol-3-yl)amino]-1,2,4-triazol-4-yl]-N-(2-fluor-2-methylpropyl)-7,8,9,10-tetrahydrobenzo[h]isochinolin-5-sulfonamid;
    3-Cyclopropyl-N-(2-fluor-2-methylpropyl)-10-[[6-(2-methyltetrazol-5-yl)pyridin-3-yl]amino]-7,8,9,10-tetrahydrobenzo[h]isochinolin-5-sulfonamid;
    5-Amino-1-[3-cyclopropyl-5-[(2-fluor-2-methylpropyl)sulfamoyl]-7,8,9,10-tetrahydrobenzo[h]isochinolin-7-yl]imidazol-4-carbonsäureethylester;
    3-Cyclopropyl-N-(2-fluor-2-methylpropyl)-7-[[5-(3-methyl-1,2,4-oxadiazol-5-yl)pyridin-3-yl]amino]-7,8,9,10-tetrahydrobenzo[h]isochinolin-5-sulfonamid;
    1-[3-Cyclopropyl-5-[(2-fluor-2-methylpropyl)sulfamoyl]-7,8,9,10-tetrahydrobenzo[h]isochinolin-7-yl]-3-(2,5-dimethylpyrazol-3-yl)harnstoff;
    1-[3-Cyclopropyl-5-[(2-fluor-2-methylpropyl)sulfamoyl]-7,8,9,10-tetrahydrobenzo[h]isochinolin-7-yl]imidazol-4-carbonsäureethylester.
  7. Pharmazeutische Zusammensetzung, umfassend eine Verbindung nach einem der Ansprüche 1 bis 6 oder ein pharmazeutisch unbedenkliches Salz davon.
  8. Verbindung nach einem der Ansprüche 1 bis 6 oder pharmazeutisch unbedenkliches Salz davon zur Verwendung in der Therapie.
  9. Verbindung nach einem der Ansprüche 1 bis 6 oder pharmazeutisch unbedenkliches Salz davon zur Verwendung in einem Verfahren zur Behandlung oder Prävention von Allergie, nichtallergischen Mastzellreaktionen, Typ-1-Hypersensibilität, Nesselsucht oder familiärer Nasennebenhöhlenentzündung.
  10. Verbindung nach einem der Ansprüche 1 bis 6 oder pharmazeutisch unbedenkliches Salz davon zur Verwendung in einem Verfahren zur Behandlung oder Prävention von Atemwegsverengung bei Asthma, lokaler Entzündung bei Ekzemen, erhöhter Schleimsekretion bei allergischer Rhinitis, Nesselsucht oder erhöhter Gefäßpermeabilität.
  11. Verbindung nach einem der Ansprüche 1 bis 6 oder pharmazeutisch unbedenkliches Salz davon zur Verwendung in einem Verfahren zur Behandlung oder Prävention von eosinophiler Granulomatose mit Polyangiitis (auch als "Churg-Strauss-Syndrom" bekannt), durch Aspirin verschlimmerter Atemwegserkrankung oder kutanem T-Zell-Lymphom.
  12. Pharmazeutische Zusammensetzung, umfassen eine Verbindung (I) nach einem der Ansprüche 1 bis 6 oder pharmazeutisch unbedenkliches Salz davon in Assoziation mit einem pharmazeutisch unbedenklichen Träger.
  13. Verbindung nach einem der Ansprüche 1 bis 6 oder pharmazeutisch unbedenkliches Salz davon zur Verwendung als Medikament.
  14. Verbindung nach einem der Ansprüche 1 bis 6 oder pharmazeutisch unbedenkliches Salz davon zur Verwendung als Medikament bei der Behandlung und/oder Prävention von Allergie, nichtallergischen Mastzellreaktionen, Typ-1-Hypersensibilität, Nesselsucht oder familiärer Nasennebenhöhlenentzündung.
  15. Verbindung nach einem der Ansprüche 1 bis 6 oder pharmazeutisch unbedenkliches Salz davon zur Verwendung bei der Behandlung oder Prävention von Allergie, nichtallergischen Mastzellreaktionen, Typ-1-Hyper-sensibilität, Nesselsucht, familiärer Nasennebenhöhlenentzündung, eosinophiler Granulomatose mit Polyangiitis (auch als "Churg-Strauss-Syndrom" bekannt), durch Aspirin verschlimmerter Atemwegserkrankung oder kutanem T-Zell-Lymphom.
EP20841927.5A 2019-12-23 2020-12-22 Tetrahydrobenzo-chinolinsulfonamidderivate als ige-modulatoren Active EP4081297B1 (de)

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GB201919212D0 (en) 2019-12-23 2020-02-05 Ucb Biopharma Sprl Dihydro-cyclopenta-isoquinoline sulfonamides derivatives
GB201919213D0 (en) 2019-12-23 2020-02-05 Ucb Biopharma Sprl Dihydrocyclopenta-Isoquinoline-Sulfanamide derivatives compounds
GB201919210D0 (en) * 2019-12-23 2020-02-05 UCB Biopharma SRL Dihydro-cyclopenta-isoquinoline derivatives

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US20230050670A1 (en) 2023-02-16
CN114845776A (zh) 2022-08-02
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